Eddie, in continuing the discussion of 1920s MS.
When I imagine a 1920s Main Street of bootleggers, speakeasies, Studebakers, etc. in a Disney park, my mental image is that of an urbanized, brownstone & art deco setting:
However, most of the artwork from this version retains very strong connections to the earlier periods (such as Victorian) and generally still feels like the classic MSUSA:
From the artwork showcased on DisneyandMore, the concept looks to have been a more subtle, than radical, departure from the MSUSA paradigm. I think this is because in order to evoke NYC or Chicago, one needs to establish verticality - the defining aspect of these cities in the 1920s.
Were you ever considering, as part of this 1920s Main Street, building taller than the 2 or so stories (or adding forced perspective, step-backed "skyscrapers") in order to create the illusion of Big City USA? I think it would be somewhat of a challenge to evoke the French love & fascination for high-rise NYC (to which I can attest) in what is required to be a fairly low-rise environment.